HCID 69506750, compound → HCID 69506811, compound

HRID 2366741Notes

Reaction equation

HRID 2366741 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(#N)C>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 69506750HCID 69506750, compound

Product 1

HCID 69506811HCID 69506811, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 5% platinum on carbon (1.2 g) and ethyl 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanecarboxylate (11.7 g, 32.7 mmol) in acetonitrile (100 mL) was placed under hydrogen pressure (3 atm, 2.1×105 Pa) on a Parr apparatus for five hours and filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure to provide 9.60 g of ethyl 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexanecarboxylate as an orange oil that solidified upon standing.

Workup

  1. customfor five hours
  2. filtrationfiltered through a layer of CELITE filter agent
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2696bcbc06034697ba77f1bfdd83b521
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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